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Studies in macrolide synthesis: A concise asymmetric synthesis of a macrolide intermediate for the erythronolides.

✍ Scribed by Ian Paterson; David D.P. Laffan; David J. Rawson


Book ID
108381639
Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
355 KB
Volume
29
Category
Article
ISSN
0040-4039

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The (9s)-macrolide 1 (P = TBS) was prepared in 14 steps (5% yield) with 63% overall ds starting from the ethyl ketone ($2. The Cl-C7 and Q-C13 segments, 3 and 4, were obtained via boron enolate aldol reactions mediated by (+)-and (-)-(Ipc)zBOTf, respectively. Conventional reduction conditions using

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